3-Methoxypropylamine → N-(3-methoxypropyl)urea

HRID 1576228Notes

Reaction equation

HRID 1576228 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[O-:7][C:8]#[N:9].[K+].C(CC(O)=O)#N.C(OC(=O)C)(=O)C>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:8]([NH2:9])=[O:7]

Participants

5

Reactant 4

HCID 16723-MethoxypropylamineHCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 11378442Potassium cyanate

Product 1

HCID 2064040N-(3-methoxypropyl)urea

Procedure

3-Methoxypropyl urea was prepared from methoxypropylamine and potassium cyanate. Seventy-six grams of this product was mixed with 43 g. of cyanoacetic acid and 100 ml. of acetic anhydride. The mixture was stirred and heated on a steam bath. When the temperature of the mixture reached 85°C., heat of reaction evolved and external cooling was applied to keep the temperature under control. After stirring for 1 hour on the steam bath, the mixture was cooled. The cyanoacetyl urea was recovered by filtration, washing with ether and drying. Yield 77.5 g., mp 128.5-130.5°.

Workup

  1. temperatureheated on a steam bath
  2. customreached 85°C.
  3. temperatureheat of reaction
  4. temperatureexternal cooling
  5. stirringAfter stirring for 1 hour on the steam bath
  6. temperaturethe mixture was cooled
  7. filtrationThe cyanoacetyl urea was recovered by filtration
  8. washwashing with ether
  9. customdrying

Sources & evidence

ORD record
ord-aab2e2c886ae4c739669fd86177dcbd8
Source dataset
uspto-grants-1976_09
Patent number
US03979518

Reaction notes

Loading…